Herbicidal sulfonamides

ABSTRACT

This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.

RELATED APPLICATIONS

This application is a continuation-in-part of my copending application U.S. Ser. No. 295,247 filed Aug. 24, 1981 (now abandoned).

BACKGROUND OF THE INVENTION

This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.

U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Y is methyl or methoxy; or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ must be hydrogen.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR2## wherein R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR3## wherein R₁ is hydrogen or lower saturated aliphatic acyl; and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR4## wherein R=H, halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R₁ is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.

Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR8## wherein R=H or CH₃.

Unexamined European Pat. No. 7687 discloses, among others, herbicidal sulfonylureas of the general structure: ##STR9## where R is H, alkyl, alkenyl, aryl, etc.;

R₆ is H or alkyl; or

R and R₆ can be taken together to form --(CH₂)₄, --(CH₂)₅ --, --(CH₂)₆ --, --CH₂ CH₂ OCH₂ CH₂ -- or --CH₂ CH₂ N(CH₃)CH₂ CH₂ --.

U.S. Ser. No. 209,307, filed Nov. 24, 1980, discloses, among others, herbicidal sulfonylureas of the general structure ##STR10## where R is H, C₁ -C₁₂ alkyl, --(CH₂ CH₂ O)--_(n'") R₁₂, CH₂ CH₂ CH₂ OR₁₂, C₃ -C₁₀ alkenyl, C₃ -C₆ alkynyl, C₃ -C₈ cycloalkyl, C₅ -C₆ cycloalkenyl, C₅ -C₈ cycloalkyl substituted with 1-3 substituents selected from 0-2 OCH₃, 0-3 CH₃ or C₂ H₅, trifluoromethylcyclohexyl, C₄ -C₁₀ cycloalkylalkyl, C₄ -C₈ cycloalkylalkyl substituted with 1-2 CH₃, CH₂ CH₂ CN, C(CH₃)₂ CN, OCH₃, OC₂ H₅, N(CH₃)₂, ##STR11## R₆ is H, C₁ -C₃ alkyl, allyl, CH₂ CN or CH₂ CH₂ CN; or

R₆ and R may be taken together as --(CH₂)₄ --, --(CH₂)₅ --, --(CH₂)₆ --, --CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ N(CH₃)CH₂ CH₂ -- or ##STR12## provided that when R is OCH₃ or OC₂ H₅, then R₆ is H or CH₃ ; when R₆ is CH₂ CH₂ CN or CH₂ CN, then R is CH₂ CH₂ CN or CH₂ CN; R and R₆ have a total number of carbon atoms ≧13 and that when NR₆ R is other than NHOCH₃, NHOC₂ H₅ or ##STR13## then R₂ is NCO, NHC(O)B, NHC(O)SB^(I), NHC(O)OB^(II), NHC(O)NHB^(III), CF₃ SO₂ NH or CH₃ SO₂ NH.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them and their method of use as general and/or selective pre-emergence and/or post-emergence herbicides and as plant growth regulants. ##STR14## wherein A is a five- or six-membered aromatic heterocycle, a five- or six-membered dihydroaromatic heterocycle or a six-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4 CH₃, 1-2 OCH₃, 0-1 SCH₃, 0-1 Cl, 0-1 N(CH₃)₂, or 0-1 CN groups;

R is H or CH₃ ;

R₁ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ;

R₂ is H or CH₃ ;

R₃ is H or CH₃ ;

R₄ is ##STR15## X is CH₃, OCH₃ or Cl; Y is H, CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ;

Y₁ is H, Cl, CH₃ or OCH₃ ; and

Z is CH, CCH₃ or N

provided that

(1) the bond between N--R and A is attached to a nitrogen or carbon atom of A;

(2) when A is a thiophene or furan ring, the bond between NR and A is not at the 2- or 5-position of the heterocycle; and

(3) when X is Cl, then Z is CH and Y is CH₃, OCH₃, NH₂, NHCH₃ or N(CH₃)₂.

Preferred for higher herbicidal activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered aromatic heterocycle containing one to three nitrogen atoms;

(2) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered dihydroaromatic heterocycle containing two nitrogen atoms;

(3) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one to four nitrogen atoms;

(4) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one or two nitrogen atoms and one oxygen or one sulfur atom;

(5) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one oxygen or one sulfur atom;

(6) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered dihydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;

(7) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered tetrahydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;

(8) Compounds of Preferred (1)-(7) wherein ##STR16## Y is CH₃ or OCH₃ ; and Z is CH or N; (9) Compounds of Preferred (8) wherein A is unsubstituted or optionally substituted with 0-4 CH₃ or 0-2 OCH₃ groups;

(10) Compounds of Preferred (9) wherein A is a pyridine, a pyrimidine or a 1,3,5-triazine;

(11) Compounds of Preferred (9) wherein A is a pyrrole, an imidazole, a pyrazole, or a 1,2,4-triazole;

(12) Compounds of Preferred (9) wherein A is an isoxazole, an oxazole, a 1,3,4-oxadiazole, a thiazole, a 1,2,3-thiadiazole, or a 1,3,4-thiadiazole;

(13) Compounds of Preferred (9) wherein A is a 4,5-dihydroimidazole, a 4,5-dihydroisoxazole, a 4,5-dihydrooxazole, a 4,5-dihydropyrazole, or a 4,5-dihydrothiazole;

(14) Compounds of Preferred (9) wherein A is a tetrahydropyrimidine, a tetrahydro-1,2,-oxazine, a tetrahydrol, 3-oxazine, or a tetrahydro-1,3-thiazine;

(15) Compounds of Preferred (10)-(14) wherein R, R₁, R₂ and R₃ are H, and A is unsubstituted, or, optionally substituted with one methyl group.

Specifically Preferred for highest herbicidal activity and/or most favorable ease of synthesis are:

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide;

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminocarbonyl]-N-(1,2,4-triazol-3-yl)benzamide;

2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1-methyl-1H-pyrazol-3-yl)benzamide;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide; and

N-(3,4-dimethylisoxazol-5-yl)-2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzamide.

Synthesis

The compounds of Formula I can be prepared from the corresponding esters by reaction with the heterocyclic amine III in the presence of an equivalent amount of trimethylaluminum according to Equation 1. ##STR17##

According to the procedure of A. Basha, M. Lipton, and S. W. Weinreb, Tetrahedron Letters, 4171 (1977), the heterocyclic amine and the trimethylaluminum are mixed in methylene chloride, followed by the addition of a methyl ester of Formula II. The mixture is then heated at reflux for 12 to 24 hours.

The product can be isolated by addition of aqueous hydrochloric acid to decompose and dissolve the aluminum complexes and salts. Direct filtration of the precipitate or separation of the methylene chloride phase followed by evaporation yields the desired product which may be purified by crystallization or column chromatography.

The preparation of esters of Formula II is described in European Patent Application No. 7687.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride) quaternary amine salts can be made by similar techniques. Detailed examples of such techniques are given in U.S. Pat. No. 4,127,405, the disclosure of which is herein incorporated by reference.

The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless otherwise indicated.

EXAMPLE 1 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide

To 1.44 g of trimethylaluminum (10 ml of a 2M solution of trimethylaluminum in toluene) in 100 ml of methylene chloride was added 2.5 g of 2-amino-4,6-dimethylpyrimidine with stirring at ambient temperature. To this mixture was added 4.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the solution refluxed for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was found to be nearly pure by thin layer chromatography (TLC) on silica gel with an eluting solvent of ethyl acetate. Trituration of the solid with methylene chloride resulted in pure product (1.8 g); m.p. 198°-199° C.; IR: 3200 cm⁻¹, NH, 1720 cm⁻¹ sulfonylurea carbonyl, 1700 cm⁻¹ amide carbonyl.

NMR: 2.2 ppm s, 6H, CH₃ on pyrimidine, 3.9 ppm s, 6H, OCH₃ on pyrimidine, 5.8 ppm, s, 1H proton in 5-position on the dimethoxypyrimidine, 6.7 ppm s, 1H, proton in 5-position of dimethylpyrimidine, 7.4-7.8 ppm and 8.0-8.4 ppm M, 4H, aromatic protons.

EXAMPLE 2 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide

To a slurry of 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 ml of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH₃)₃). Evolution of methane gas was seen and the solution became homogeneous. 2-Aminopyrimidine (1.9 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.35 g, m.p. 206°-207° C., IR: 1710 cm⁻¹ sulfonylurea carbonyl, 1680 cm⁻¹ amide carbonyl.

NMR: in TFA, 2.8 ppm, CH₃ on pyrimidine, 4.3 ppm, OCH₃ on pyrimidine, 6.8 ppm, proton in 5-position of pyrimidine, 7.8-8.0 ppm and 8.4-8.6 ppm, aromatic protons.

EXAMPLE 3 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,2,4-triazol-3-yl)benzamide

To a slurry of 4.0 g of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 ml of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH₃)₃). Evolution of methane gas was seen. 3-Amino-1,2,4-triazole (1.7 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 0.63 g, m.p. 176°-179° C. NMR in TFA 2.9 ppm s, CH₃ on triazine, 4.4 ppm s, OCH₃ on triazine, 7.8-8.0 ppm and 8.2-8.5 ppm M, aromatic.

EXAMPLE 4 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide

To a solution of 2-aminotriazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH₃)₃) by syringe. Evolution of methane gas was seen and the solution became homogeneous. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the homogeneous solution was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product isolated by filtration, 1.42 g, m.p. 185°-187° C. IR: 1690 cm⁻¹ and 1700 cm⁻¹ unresolved double carbonyl, NMR: in TFA 2.7 ppm s, CH₃ pyrimidine, 4.2 ppm s, OCH₃ on pyrimidine, 6.7 ppm s, proton in 5-position on pyrimidine, 7.8-8.0 ppm and 8.4-8.5 ppm M, aromatic, 7.6, 7.7 ppm D, thiazole.

EXAMPLE 5 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide

To a solution of 2-amino-1,3,4-thiadiazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH₃)₃) by syringe. Evolution of methane gas was seen from the homogeneous solution. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl-2-methoxycarbonylbenzenesulfonamide and the slurry was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.61 g, m.p. 172°-173° C. IR: 1700 cm⁻¹ unresolved carbonyls, NMR: in TFA 2.9 ppm s, CH₃ pyrimidine, 4.4 ppm s, OCH₃ on pyrimidine, 5.4 ppm s, thiadiazole, 6.9 ppm s, proton in 5-position on pyrimidine, 8.1 and 8.5 ppm M, aromatic.

Using the procedures and examples described above and choosing the appropriate compounds of Formulae II and III (as illustrated in Table I), the compounds described in Tables II-VII may be prepared.

                  TABLE I                                                          ______________________________________                                         A: Structures                                                                  ______________________________________                                          ##STR18##   1                                                                                        ##STR19##     2                                          ##STR20##   3                                                                                        ##STR21##     4                                          ##STR22##   5                                                                                        ##STR23##     6                                          ##STR24##   7                                                                                        ##STR25##     8                                          ##STR26##   9                                                                                        ##STR27##     10                                         ##STR28##   11                                                                                       ##STR29##     12                                         ##STR30##   13                                                                                       ##STR31##     14                                         ##STR32##   15                                                                                       ##STR33##     16                                         ##STR34##   17                                                                                       ##STR35##     18                                         ##STR36##   19                                                                                       ##STR37##     20                                         ##STR38##   21                                                                                       ##STR39##     22                                         ##STR40##   23                                                                                       ##STR41##     24                                         ##STR42##   25                                                                                       ##STR43##     26                                         ##STR44##   27                                                                                       ##STR45##     28                                         ##STR46##   29                                                                                       ##STR47##     30                                         ##STR48##   31                                                                                       ##STR49##     32                                         ##STR50##   33                                                                                       ##STR51##     34                                         ##STR52##   35                                                                                       ##STR53##     36                                         ##STR54##   37                                                                                       ##STR55##     38                                         ##STR56##   39                                                                                       ##STR57##     40                                         ##STR58##   41                                                                                       ##STR59##     42                                         ##STR60##   43                                                                                       ##STR61##     44                                         ##STR62##   45                                                                                       ##STR63##     46                                         ##STR64##   47                                                                                       ##STR65##     48                                         ##STR66##   49                                                                                       ##STR67##     50                                         ##STR68##   51                                                                                       ##STR69##     52                                         ##STR70##   53                                                                                       ##STR71##     54                                         ##STR72##   55                                                                                       ##STR73##     56                                         ##STR74##   57                                                                                       ##STR75##     58                                         ##STR76##   59                                                                                       ##STR77##     60                                         ##STR78##   61                                                                                       ##STR79##     62                                         ##STR80##   63                                                                                       ##STR81##     64                                         ##STR82##   65                                                                                       ##STR83##     66                                         ##STR84##   67                                                                                       ##STR85##     68                                         ##STR86##   69                                                                                       ##STR87##     70                                         ##STR88##   71                                                                                       ##STR89##     72                                         ##STR90##   73                                                                                       ##STR91##     74                                        ______________________________________                                    

                                      TABLE II                                     __________________________________________________________________________      ##STR92##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p. (°C.)                       __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      2  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     3  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     4  H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     5  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub. 3                                    5  H  5-Cl H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     6  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             208-211                                 6  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            203-206                                 7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      8  H  5-F  H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     8  H  5-Br H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     9  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      10 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     11 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                      12 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     12 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                                                             226-230                                 12 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                                                            180-182                                 13 H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          OCH.sub.3                                     16 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     17 H  5-F  H  H  --    --    CH.sub.3                                                                           CH.sub.3                                      18 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                      19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub. 3                                                                          CH.sub.3                                                                             149-151                                 19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                            173-175                                 20 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      21 H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      22 H  5-NO.sub.2                                                                          H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     23 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     26 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     28 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      29 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     30 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  5-Cl H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     31 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             192-194                                 32 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            185-187                                 32 H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     33 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      33 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     34 H  H    H  H  2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     34 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     34 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                                                             168-170                                 35 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     35 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                                                            172-173                                 35 CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     35 H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     35 H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                                                          OCH.sub.3                                     36 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      36 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     36 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     37 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      37 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     37 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     39 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      39 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     40 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      40 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  4-Cl  --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  4-CN  --    OCH.sub.3                                                                          CH.sub.3                                      41 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     42 H  H    H  H  4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      42 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     43 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             215-216                                 43 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            206-207                                 43 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  5-CN  H     CH.sub.3                                                                           OCH.sub.3                                     44 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      44 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     44 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     45 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      45 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     45 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      46 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     46 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      47 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     47 H  H    H  H  6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      48 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     49 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             190-191                                 49 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                            184-185                                 49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                            198-199                                 49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                             188-190                                 49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                            202-204                                 49 H  H    H  H  4-Cl  6-Cl  CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-Cl  6-CN  CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      51 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     51 H  H    H  H  2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      52 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     53 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      53 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     53 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                     54 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      54 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     54 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     55 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      55 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     55 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     56 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      56 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     56 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     56 H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     57 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     57 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     58 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     58 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     59 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      59 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     59 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     59 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     59 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     60 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     61 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     61 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     62 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     62 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     63 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     63 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     64 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     64 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     65 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     66 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     67 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     67 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     68 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     68 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     69 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     69 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     70 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     70 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     71 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     Cl  OCH.sub.3                                     32 H  H    H  H  H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                               32 H  H    H  H  H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                              32 H  H    H  H  H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                            35 H  H    H  H  H     --    Cl  CH.sub.3                                      35 H  H    H  H  H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                               35 H  H    H  H  H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                              35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            35 H  H    H  H  H     --    CH.sub.3                                                                           H                                             32 H  H    H  H  H     --    Cl  NH.sub.2                                      32 H  H    H  H  H     --    Cl  NHCH.sub.3                                    35 H  H    H  H  H     --    Cl  N(CH.sub.3).sub.2                             __________________________________________________________________________

                                      TABLE III                                    __________________________________________________________________________      ##STR93##                                                                     A R R.sub.1                                                                             R.sub.2                                                                          R.sub.3                                                                          R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p. (°C).                           __________________________________________________________________________     1 H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          1 H H    H H 4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                          2 H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         2 H H    H H 5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                          3 H H    H H 2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         3 H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         4 H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         5 H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         5 H 5-Cl H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         6 H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          6 H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                                                            194-197                                     7 H H    H H 3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                          8 H 5-F  H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         8 H 5-Br H H 4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         9 H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          10                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         11                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         12                                                                               H H    H H 5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                          12                                                                               H H    H H 5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         12                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          12                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                                                            176-179                                     13                                                                               H H    H H 3-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                         14                                                                               H H    H H 3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                          15                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub. 3                                         15                                                                               H H    H H CH.sub.3                                                                             --    OCH.sub.3                                                                          OCH.sub.3                                         16                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         17                                                                               H 5-F  H H --    --    CH.sub.3                                                                           CH.sub.3                                          18                                                                               H H    H H CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                          19                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                          19                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                            142-144                                     20                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          21                                                                               H 5-OCH.sub.3                                                                         H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         22                                                                               H 5-CF.sub.3                                                                          H H H     H     CH.sub.3                                                                           CH.sub.3                                          22                                                                               H 5-NO.sub.2                                                                          H H H     --    CH.sub.3                                                                           OCH.sub.3                                         23                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         24                                                                               H H    H H 5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                          25                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          25                                                                               H H    H H CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                         26                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          27                                                                               H 5-NO.sub.2                                                                          H H H     --    OCH.sub. 3                                                                         OCH.sub.3                                         28                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         29                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          29                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         29                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         30                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          31                                                                               H 5-Cl H H H     --    CH.sub.3                                                                           CH.sub.3                                          31                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         31                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         32                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          32                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         32                                                                               H H    H H 4-CH.sub.3                                                                           H     OCH.sub.3                                                                          OCH.sub.3                                         32                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         33                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          33                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         33                                                                               H H    H H 2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                         34                                                                               H H    H H 2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         34                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         34                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          35                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          35                                                                               H H    H H 5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         35                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         35                                                                               CH.sub.3                                                                         H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         35                                                                               H H    CH.sub.3                                                                         H H     --    OCH.sub.3                                                                          OCH.sub.3                                         35                                                                               H H    H CH.sub.3                                                                         H     --    OCH.sub.3                                                                          OCH.sub.3                                         36                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          36                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         36                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         37                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          37                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         37                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         38                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         38                                                                               H H    H H CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                         39                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub. 3                                         39                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         40                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          40                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         41                                                                               H H    H H 4-Cl  --    CH.sub.3                                                                           CH.sub.3                                          41                                                                               H H    H H 4-CN  --    OCH.sub.3                                                                          CH.sub.3                                          41                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          41                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         41                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         42                                                                               H H    H H 4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                         42                                                                               H H    H H 5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         42                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          42                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         42                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         43                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          43                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                                                            161-163                                     43                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         43                                                                               H H    H H 4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         43                                                                               H H    H H 3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         43                                                                               H H    H H 3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         43                                                                               H H    H H 4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           OCH.sub.3                                         43                                                                               H H    H H 5-CN  H     CH.sub.3                                                                           OCH.sub.3                                         44                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          44                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         44                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         45                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          45                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         45                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         46                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          46                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         46                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         46                                                                               H H    H H 5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         46                                                                               H H    H H 5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         47                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          47                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         47                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         47                                                                               H H    H H 6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         47                                                                               H H    H H 3-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                             48                                                                               H H    H H 5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         48                                                                               H H    H H 5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                         48                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          48                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         48                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         49                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          49                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         49                                                                               H H    H H 4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                          49                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         49                                                                               H H    H H 4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                            172-173                                     49                                                                               H H    H H 4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         49                                                                               H H    H H 4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                          49                                                                               H H    H H 4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                            194-196                                     49                                                                               H H    H H 4-Cl  6-Cl  CH.sub.3                                                                           OCH.sub.3                                         49                                                                               H H    H H 4-Cl  4-N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           OCH.sub.3                                         49                                                                               H H    H H 4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                         49                                                                               H H    H H 4-Cl  6-CN  CH.sub.3                                                                           OCH.sub.3                                         50                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          50                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         50                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         50                                                                               H H    H H 2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                         50                                                                               H H    H H 2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                         50                                                                               H H    H H 2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                         51                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          51                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         51                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         51                                                                               H H    H H 2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         51                                                                               H H    H H 5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                         51                                                                               H H    H H OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                         52                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          52                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         52                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         52                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                         52                                                                               H H    H H CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                         52                                                                               H H    H H OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                         53                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          53                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         53                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         53                                                                               H H    H H 5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         54                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          54                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         54                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         55                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          55                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         55                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         56                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          56                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         56                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         56                                                                               H H    H H 6-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                         57                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         57                                                                               H H    H H 4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         58                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         58                                                                               H H    H H 4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         59                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.3                                          59                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         59                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         59                                                                               H H    H H 4-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                         59                                                                               H H    H H 5-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                         60                                                                               H H    H H 4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         61                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         61                                                                               H H    H H 5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                         62                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         62                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         63                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub. 3                                        63                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         64                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         64                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         65                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         66                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         67                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         67                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         68                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         68                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         69                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         69                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         70                                                                               H H    H H H     --    CH.sub.3                                                                           OCH.sub.3                                         70                                                                               H H    H H H     --    OCH.sub.3                                                                          OCH.sub.3                                         71                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          71                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         71                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         71                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub. 3                                                                          CH.sub.3                                          71                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                         71                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                         71                                                                               H H    H H CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                         71                                                                               H H    H H OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                         72                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          72                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         72                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         72                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                          72                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                         72                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                         72                                                                               H H    H H CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                         72                                                                               H H    H H OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                         73                                                                               H H    H H H     H     CH.sub.3                                                                           CH.sub.3                                          73                                                                               H H    H H H     H     CH.sub.3                                                                           OCH.sub.3                                         73                                                                               H H    H H H     H     OCH.sub.3                                                                          OCH.sub.3                                         73                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                          73                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                         73                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                         73                                                                               H H    H H CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                         73                                                                               H H    H H OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                         74                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                          74                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                         74                                                                               H H    H H CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                         32                                                                               H H    H H H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                                   32                                                                               H H    H H H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  32                                                                               H H    H H H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                35                                                                               H H    H H H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                                   35                                                                               H H    H H H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                                  35                                                                               H H    H H H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                35                                                                               H H    H H H     --    CH.sub.3                                                                           H                                                 __________________________________________________________________________

                                      TABLE IV                                     __________________________________________________________________________      ##STR94##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p. (°C.)                       __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      2  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     3  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     4  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      5  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     5  H  5-Cl H  H  H     H     CH.sub.3                                                                           H                                             6  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      6  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      8  H  5-F  H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      8  H  5-Br H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     9  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      10 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     11 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                      12 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                             12 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      12 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     13 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                             14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     16 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     17 H  5-F  H  H  --    --    CH.sub.3                                                                           CH.sub.3                                      18 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                      19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     20 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      21 H  5-OCH.sub.3                                                                         H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      22 H  5-NO.sub.2                                                                          H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     23 H  H    H  H  H     --    CH.sub.3                                                                           H                                             24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     26 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                                                          CH.sub.3                                      28 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      29 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     30 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  5-Cl H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     31 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      32 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     32 H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           H                                             32 H  H    H  H  H     H     CH.sub.3                                                                           H                                             33 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      33 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     34 H  H    H  H  2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     34 H  H    H  H  H     --    CH.sub.3                                                                           H                                             34 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      35 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     35 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     35 CH.sub.3                                                                          H    H  H  H     --    CH.sub.3                                                                           H                                             35 H  H    CH.sub.3                                                                          H  H     --    CH.sub.3                                                                           CH.sub.3                                      35 H  H    H  CH.sub.3                                                                          H     --    CH.sub.3                                                                           CH.sub.3                                      36 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      36 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     36 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     37 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      37 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     37 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     39 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      39 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     40 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      40 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  4-Cl  --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  4-CN  --    OCH.sub.3                                                                          CH.sub.3                                      41 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     41 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  H     --    CH.sub.3                                                                           H                                             42 H  H    H  H  4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      42 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     43 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      43 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  H     H     CH.sub.3                                                                           H                                             43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           CH.sub.3                                      43 H  H    H  H  5-CN  H     CH.sub.3                                                                           CH.sub.3                                      44 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      44 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     44 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     45 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      45 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     45 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      46 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     46 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                             47 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      47 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     47 H  H    H  H  6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                             48 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      48 H  H    H  H  5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      48 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     CH.sub.3                                                                           H                                             49 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                             49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-Cl  6-Cl  CH.sub.3                                                                           H                                             49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           H                                             49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  4-Cl  6-CN  CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      51 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     51 H  H    H  H  2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           H                                             51 H  H    H  H  OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      52 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                             52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      53 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      53 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     53 H  H    H  H  H     H     CH.sub.3                                                                           H                                             53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      54 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      54 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     54 H  H    H  H  H     H     CH.sub.3                                                                           H                                             55 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      55 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     55 H  H    H  H  H     H     CH.sub.3                                                                           H                                             56 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      56 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     56 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     56 H  H    H  H  6-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub. 3                                     57 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     57 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      58 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     58 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      59 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      59 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     59 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     59 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      59 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                             60 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      61 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     61 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      62 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     62 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     63 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     63 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      64 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     64 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      65 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     66 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      67 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     67 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      68 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     68 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      69 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     69 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      70 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     70 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     71 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                             71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                             72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  CH.sub. 3                                                                            CH.sub.3                                                                             CH.sub.3                                                                           H                                             73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                      74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                             32 H  H    H  H  H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                               32 H  H    H  H  H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                              32 H  H    H  H  H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                            35 H  H    H  H  H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                               35 H  H    H  H  H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                              35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR95##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              Y.sub.1                                                                             m.p. (°C.)                            __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                          1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                          2  H  H    H  H  H     H     OCH.sub.3                                         2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                          3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         3  H  H    H  H  H     H     OCH.sub.3                                         4  H  H    H  H  H     H     OCH.sub.3                                         5  H  H    H  H  H     H     OCH.sub.3                                         5  H  5-Cl H  H  H     H     OCH.sub.3                                         6  H  H    H  H  H     H     CH.sub. 3                                         6  H  H    H  H  H     H     OCH.sub.3                                         7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                          8  H  5-F  H  H  H     H     OCH.sub.3                                         8  H  5-Br H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         9  H  H    H  H  H     H     CH.sub.3                                          10 H  H    H  H  H     H     OCH.sub.3                                         11 H  H    H  H  H     H     OCH.sub.3                                         12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                          12 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         12 H  H    H  H  H     --    CH.sub.3                                          12 H  H    H  H  H     --    OCH.sub.3                                         13 H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                         14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                          15 H  H    H  H  H     --    CH.sub.3                                          15 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         16 H  H    H  H  H     --    OCH.sub.3                                         17 H  5-F  H  H  --    --    CH.sub.3                                          18 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                          19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          19 H  H    H  H  CH.sub. 3                                                                            CH.sub.3                                                                             OCH.sub.3                                         20 H  H    H  H  H     H     CH.sub.3                                          21 H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                         22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                          22 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         23 H  H    H  H  H     --    OCH.sub.3                                         24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                          25 H  H    H  H  H     --    CH.sub.3                                          25 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         26 H  H    H  H  H     --    CH.sub.3                                          27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         28 H  H    H  H  H     --    OCH.sub.3                                         29 H  H    H  H  H     --    CH.sub.3                                          29 H  H    H  H  H     --    OCH.sub.3                                         30 H  H    H  H  H     --    CH.sub.3                                          31 H  5-Cl H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    OCH.sub.3                                         32 H  H    H  H  H     H     CH.sub.3                                          32 H  H    H  H  H     H     OCH.sub.3                                         32 H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         33 H  H    H  H  H     --    CH.sub.3                                          33 H  H    H  H  H     --    OCH.sub.3                                         33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  H     --    OCH.sub.3                                         34 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         35 H  H    H  H  H     --    OCH.sub.3                                         35 CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                         35 H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                         35 H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                         36 H  H    H  H  H     --    CH.sub.3                                          36 H  H    H  H  H     --    OCH.sub.3                                         37 H  H    H  H  H     --    CH.sub.3                                          37 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         39 H  H    H  H  H     --    CH.sub.3                                          39 H  H    H  H  H     --    OCH.sub.3                                         40 H  H    H  H  H     --    CH.sub.3                                          40 H  H    H  H  H     --    OCH.sub.3                                         41 H  H    H  H  4-Cl  --    CH.sub.3                                          41 H  H    H  H  4-CN  --    CH.sub.3                                          41 H  H    H  H  H     --    CH.sub.3                                          41 H  H    H  H  H     --    OCH.sub.3                                         42 H  H    H  H  4-Cl  --    OCH.sub.3                                         42 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         42 H  H    H  H  H     --    CH.sub.3                                          42 H  H    H  H  H     --    OCH.sub.3                                         43 H  H    H  H  H     H     CH.sub.3                                          43 H  H    H  H  H     H     OCH.sub.3                                         43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     OCH.sub.3                                         43 H  H    H  H  5-CN  H     OCH.sub.3                                         44 H  H    H  H  H     H     CH.sub.3                                          44 H  H    H  H  H     H     OCH.sub.3                                         45 H  H    H  H  H     H     CH.sub.3                                          45 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  H     H     CH.sub.3                                          46 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         47 H  H    H  H  H     H     CH.sub.3                                          47 H  H    H  H  H     H     OCH.sub.3                                         47 H  H    H  H  6-CH.sub.3                                                                           H     OCH.sub.3                                         47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         48 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         48 H  H    H  H  5-Cl  H     OCH.sub.3                                         48 H  H    H  H  H     H     CH.sub.3                                          48 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  H     H     CH.sub.3                                          49 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                          49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                          49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-Cl  OCH.sub.3                                         49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-CN  OCH.sub.3                                         50 H  H    H  H  H     H     CH.sub.3                                          50 H  H    H  H  H     H     OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  OCH.sub.3                                         51 H  H    H  H  H     H     CH.sub.3                                          51 H  H    H  H  H     H     OCH.sub.3                                         51 H  H    H  H  2-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  OCH.sub.3                                                                            H     OCH.sub.3                                         52 H  H    H  H  H     H     CH.sub.3                                          52 H  H    H  H  H     H     OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         53 H  H    H  H  H     H     CH.sub.3                                          53 H  H    H  H  H     H     OCH.sub.3                                         53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         54 H  H    H  H  H     H     CH.sub.3                                          54 H  H    H  H  H     H     OCH.sub.3                                         55 H  H    H  H  H     H     CH.sub.3                                          55 H  H    H  H  H     H     OCH.sub.3                                         56 H  H    H  H  H     --    CH.sub.3                                          56 H  H    H  H  H     --    OCH.sub.3                                         56 H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                         57 H  H    H  H  H     --    OCH.sub.3                                         57 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         58 H  H    H  H  H     --    OCH.sub.3                                         58 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  H     --    CH.sub.3                                          59 H  H    H  H  H     --    OCH.sub.3                                         59 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         60 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         61 H  H    H  H  H     --    OCH.sub.3                                         61 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         62 H  H    H  H  H     --    CH.sub.3                                          62 H  H    H  H  H     --    OCH.sub.3                                         63 H  H    H  H  H     --    CH.sub.3                                          63 H  H    H  H  H     --    OCH.sub.3                                         64 H  H    H  H  H     --    CH.sub.3                                          64 H  H    H  H  H     --    OCH.sub.3                                         65 H  H    H  H  H     --    OCH.sub.3                                         66 H  H    H  H  H     --    OCH.sub.3                                         67 H  H    H  H  H     --    CH.sub.3                                          67 H  H    H  H  H     --    OCH.sub.3                                         68 H  H    H  H  H     --    CH.sub.3                                          68 H  H    H  H  H     --    OCH.sub.3                                         69 H  H    H  H  H     --    CH.sub.3                                          69 H  H    H  H  H     --    OCH.sub.3                                         70 H  H    H  H  H     --    CH.sub.3                                          70 H  H    H  H  H     --    OCH.sub.3                                         71 H  H    H  H  H     H     CH.sub.3                                          71 H  H    H  H  H     H     OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          71 H  H    H  H  CH.sub.3                                                                             CH.sub. 3                                                                            OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  H     H     CH.sub.3                                          72 H  H    H  H  H     H     OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  H     H     CH.sub.3                                          73 H  H    H  H  H     H     OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         32 H  H    H  H  H     H     Cl                                                32 H  H    H  H  H     H     H                                                 35 H  H    H  H  H     --    Cl                                                35 H  H    H  H  H     --    H                                                 __________________________________________________________________________

                  TABLE VI                                                         ______________________________________                                          ##STR96##                                                                                                                 m.p.                               A R                                                                              R.sub.1 R.sub.2  R.sub.3                                                                             R.sub.5                                                                             R.sub.6 Y.sub.1 (°C.)                      ______________________________________                                          1 H  H        H      H    H       H       CH.sub.3                             1 H  H        H      H    4-CH.sub.3                                                                             H       CH.sub.3                             2 H  H        H      H    H       H       OCH.sub.3                            2 H  H        H      H    5-CH.sub.3                                                                             H       CH.sub.3                             3 H  H        H      H    2-CH.sub.3                                                                             5-CH.sub.3                                                                             OCH.sub.3                            3 H  H        H      H    H       H       OCH.sub.3                            4 H  H        H      H    H       H       OCH.sub.3                            5 H  H        H      H    H       H       OCH.sub.3                            5 H  5-Cl     H      H    H       H       OCH.sub.3                            6 H  H        H      H    H       H       CH.sub.3                             6 H  H        H      H    H       H       OCH.sub.3                            7 H  H        H      H    3-CH.sub.3                                                                             4-CH.sub.3                                                                             CH.sub.3                             8 H  5-F      H      H    H       H       OCH.sub.3                            8 H  5-Br     H      H    4-CH.sub.3                                                                             H       OCH.sub.3                            9 H  H        H      H    H       H       CH.sub.3                            10 H  H        H      H    H       H       OCH.sub.3                           11 H  H        H      H    H       H       OCH.sub.3                           12 H  H        H      H    5-SCH.sub.3                                                                            --      CH.sub.3                            12 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           12 H  H        H      H    H       --      CH.sub.3                            12 H  H        H      H    H       --      OCH.sub.3                           13 H  H        H      H    3-CH.sub.3                                                                             --      OCH.sub.3                           14 H  H        H      H    3-CH.sub.3                                                                             --      CH.sub.3                            15 H  H        H      H    H       --      CH.sub.3                            15 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           16 H  H        H      H    H       --      OCH.sub.3                           17 H  5-F      H      H    --      --      CH.sub.3                            18 H  H        H      H    CH.sub.3                                                                               --      CH.sub.3                            19 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            19 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           20 H  H        H      H    H       H       CH.sub.3                            21 H  5-OCH.sub.3                                                                             H      H    H       H       OCH.sub.3                           22 H  5-CF.sub.3                                                                              H      H    H       H       CH.sub.3                            22 H  5-NO.sub.2                                                                              H      H    H       --      OCH.sub.3                           23 H  H        H      H    H       --      OCH.sub.3                           24 H  H        H      H    5-CH.sub.3                                                                             --      CH.sub.3                            25 H  H        H      H    H       --      CH.sub.3                            25 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           26 H  H        H      H    H       --      CH.sub.3                            27 H  5-NO.sub.2                                                                              H      H    H       --      OCH.sub.3                           28 H  H        H      H    H       --      OCH.sub.3                           29 H  H        H      H    H       --      CH.sub.3                            29 H  H        H      H    H       --      OCH.sub.3                           30 H  H        H      H    H       --      CH.sub.3                            31 H  5-Cl     H      H    H       --      CH.sub.3                            31 H  H        H      H    H       --      CH.sub.3                            31 H  H        H      H    H       --      OCH.sub.3                           32 H  H        H      H    H       H       CH.sub.3                            32 H  H        H      H    H       H       OCH.sub.3                           32 H  H        H      H    4-CH.sub.3                                                                             H       OCH.sub.3                           33 H  H        H      H    H       --      CH.sub.3                            33 H  H        H      H    H       --      OCH.sub.3                           33 H  H        H      H    2-CH.sub.3                                                                             --      OCH.sub.3                           34 H  H        H      H    2-CH.sub.3                                                                             --      OCH.sub.3                           34 H  H        H      H    H       --      OCH.sub.3                           34 H  H        H      H    H       --      CH.sub.3                            35 H  H        H      H    H       --      CH.sub.3                            35 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           35 H  H        H      H    H       --      OCH.sub.3                           35 CH.sub.3                                                                          H        H      H    H       --      OCH.sub.3                           35 H  H        CH.sub.3                                                                              H    H       --      OCH.sub.3                           35 H  H        H      CH.sub.3                                                                            H       --      OCH.sub.3                           36 H  H        H      H    H       --      CH.sub.3                            36 H  H        H      H    H       --      OCH.sub.3                           37 H  H        H      H    H       --      CH.sub.3                            37 H  H        H      H    H       --      OCH.sub.3                           38 H  H        H      H    H       --      OCH.sub.3                           38 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           39 H  H        H      H    H       --      CH.sub.3                            39 H  H        H      H    H       --      OCH.sub.3                           40 H  H        H      H    H       --      CH.sub.3                            40 H  H        H      H    H       --      OCH.sub.3                           41 H  H        H      H    4-Cl    --      CH.sub.3                            41 H  H        H      H    4-CN    --      CH.sub.3                            41 H  H        H      H    H       --      CH.sub.3                            41 H  H        H      H    H       --      OCH.sub.3                           42 H  H        H      H    4-Cl    --      OCH.sub.3                           42 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           42 H  H        H      H    H       --      CH.sub.3                            42 H  H        H      H    H       --      OCH.sub.3                           43 H  H        H      H    H       H       CH.sub.3                            43 H  H        H      H    H       H       OCH.sub.3                           43 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    3-Cl    5-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    3-CH.sub.3                                                                             5-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    4-N(CH.sub.3).sub.2                                                                    H       OCH.sub.3                           43 H  H        H      H    5-CN    H       OCH.sub.3                           44 H  H        H      H    H       H       CH.sub.3                            44 H  H        H      H    H       H       OCH.sub.3                           45 H  H        H      H    H       H       CH.sub.3                            45 H  H        H      H    H       H       OCH.sub.3                           46 H  H        H      H    H       H       CH.sub.3                            46 H  H        H      H    H       H       OCH.sub.3                           46 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           46 H  H        H      H    5-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           47 H  H        H      H    H       H       CH.sub.3                            47 H  H        H      H    H       H       OCH.sub.3                           47 H  H        H      H    6-CH.sub.3                                                                             H       OCH.sub.3                           47 H  H        H      H    3-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           48 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           48 H  H        H      H    5-Cl    H       OCH.sub.3                           48 H  H        H      H    H       H       CH.sub.3                            48 H  H        H      H    H       H       OCH.sub.3                           49 H  H        H      H    H       H       CH.sub.3                            49 H  H        H      H    H       H       OCH.sub.3                           49 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             CH.sub.3                            49 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           49 H  H        H      H    4-OCH.sub.3                                                                            6-OCH.sub.3                                                                            CH.sub.3                            49 H  H        H      H    4-OCH.sub.3                                                                            6-OCH.sub.3                                                                            OCH.sub.3                           49 H  H        H      H    4-Cl    6-Cl    OCH.sub.3                           49 H  H        H      H    4-Cl    4-N(CH.sub.3).sub.2                                                                    OCH.sub.3                           49 H  H        H      H    4-OCH.sub.3                                                                            6-SCH.sub.3                                                                            OCH.sub.3                           49 H  H        H      H    4-Cl    6-CN    OCH.sub.3                           50 H  H        H      H    H       H       CH.sub.3                            50 H  H        H      H    H       H       OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-OCH.sub.3                                                                            OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-Cl    OCH.sub.3                           51 H  H        H      H    H       H       CH.sub.3                            51 H  H        H      H    H       H       OCH.sub.3                           51 H  H        H      H    2-CH.sub.3                                                                             H       OCH.sub.3                           51 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           51 H  H        H      H    OCH.sub.3                                                                              H       OCH.sub.3                           52 H  H        H      H    H       H       CH.sub.3                            52 H  H        H      H    H       H       OCH.sub.3                           52 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           52 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           52 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           53 H  H        H      H    H       H       CH.sub.3                            53 H  H        H      H    H       H       OCH.sub.3                           53 H  H        H      H    5-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           54 H  H        H      H    H       H       CH.sub.3                            54 H  H        H      H    H       H       OCH.sub.3                           55 H  H        H      H    H       H       CH.sub.3                            55 H  H        H      H    H       H       OCH.sub.3                           56 H  H        H      H    H       --      CH.sub.3                            56 H  H        H      H    H       --      OCH.sub.3                           56 H  H        H      H    6-CH.sub.3                                                                             --      OCH.sub.3                           57 H  H        H      H    H       --      OCH.sub.3                           57 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           58 H  H        H      H    H       --      OCH.sub.3                           58 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           59 H  H        H      H    H       --      CH.sub.3                            59 H  H        H      H    H       --      OCH.sub.3                           59 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           59 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           60 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           61 H  H        H      H    H       --      OCH.sub.3                           61 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           62 H  H        H      H    H       --      CH.sub.3                            62 H  H        H      H    H       --      OCH.sub.3                           63 H  H        H      H    H       --      CH.sub.3                            63 H  H        H      H    H       --      OCH.sub.3                           64 H  H        H      H    H       --      CH.sub.3                            64 H  H        H      H    H       --      OCH.sub.3                           65 H  H        H      H    H       --      OCH.sub.3                           66 H  H        H      H    H       --      OCH.sub.3                           67 H  H        H      H    H       --      CH.sub.3                            67 H  H        H      H    H       --      OCH.sub.3                           68 H  H        H      H    H       --      CH.sub.3                            68 H  H        H      H    H       --      OCH.sub.3                           69 H  H        H      H    H       --      CH.sub.3                            69 H  H        H      H    H       --      OCH.sub.3                           70 H  H        H      H    H       --      CH.sub.3                            70 H  H        H      H    H       --      OCH.sub.3                           71 H  H        H      H    H       H       CH.sub.3                            71 H  H        H      H    H       H       OCH.sub.3                           71 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            71 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           71 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           71 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           72 H  H        H      H    H       H       CH.sub.3                            72 H  H        H      H    H       H       OCH.sub.3                           72 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            72 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           72 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           72 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           73 H  H        H      H    H       H       CH.sub.3                            73 H  H        H      H    H       H       OCH.sub.3                           73 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            73 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           73 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           73 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           74 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            74 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           32 H  H        H      H    H       H       Cl                                  32 H  H        H      H    H       H       H                                   35 H  H        H      H    H       --      Cl                                  35 H  H        H      H    H       --      H                                   ______________________________________                                    

                  TABLE VII                                                        ______________________________________                                          ##STR97##                                                                                                                 m.p.                               A R                                                                              R.sub.1 R.sub.2  R.sub.3                                                                             R.sub.5                                                                             R.sub.6 Y.sub.1 (°C.)                      ______________________________________                                          1 H  H        H      H    H       H       CH.sub.3                             1 H  H        H      H    4-CH.sub.3                                                                             H       CH.sub.3                             2 H  H        H      H    H       H       OCH.sub.3                            2 H  H        H      H    5-CH.sub.3                                                                             H       CH.sub.3                             3 H  H        H      H    2-CH.sub.3                                                                             5-CH.sub.3                                                                             OCH.sub.3                            3 H  H        H      H    H       H       OCH.sub.3                            4 H  H        H      H    H       H       OCH.sub.3                            5 H  H        H      H    H       H       OCH.sub.3                            5 H  5-Cl     H      H    H       H       OCH.sub.3                            6 H  H        H      H    H       H       CH.sub.3                             6 H  H        H      H    H       H       OCH.sub.3                            7 H  H        H      H    3-CH.sub.3                                                                             4-CH.sub.3                                                                             CH.sub.3                             8 H  5-F      H      H    H       H       OCH.sub.3                            8 H  5-Br     H      H    4-CH.sub.3                                                                             H       OCH.sub.3                            9 H  H        H      H    H       H       CH.sub.3                            10 H  H        H      H    H       H       OCH.sub.3                           11 H  H        H      H    H       H       OCH.sub.3                           12 H  H        H      H    5-SCH.sub.3                                                                            --      CH.sub.3                            12 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           12 H  H        H      H    H       --      CH.sub.3                            12 H  H        H      H    H       --      OCH.sub.3                           13 H  H        H      H    3-CH.sub.3                                                                             --      OCH.sub.3                           14 H  H        H      H    3-CH.sub.3                                                                             --      CH.sub.3                            15 H  H        H      H    H       --      CH.sub.3                            15 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           16 H  H        H      H    H       --      OCH.sub.3                           17 H  5-F      H      H    --      --      CH.sub.3                            18 H  H        H      H    CH.sub.3                                                                               --      CH.sub.3                            19 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            19 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           20 H  H        H      H    H       H       CH.sub.3                            21 H  5-OCH.sub.3                                                                             H      H    H       H       OCH.sub.3                           22 H  5-CF.sub.3                                                                              H      H    H       H       CH.sub.3                            22 H  5-NO.sub.2                                                                              H      H    H       --      OCH.sub.3                           23 H  H        H      H    H       --      OCH.sub.3                           24 H  H        H      H    5-CH.sub.3                                                                             --      CH.sub.3                            25 H  H        H      H    H       --      CH.sub.3                            25 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           26 H  H        H      H    H       --      CH.sub.3                            27 H  5-NO.sub.2                                                                              H      H    H       --      OCH.sub.3                           28 H  H        H      H    H       --      OCH.sub.3                           29 H  H        H      H    H       --      CH.sub.3                            29 H  H        H      H    H       --      OCH.sub.3                           30 H  H        H      H    H       --      CH.sub.3                            31 H  5-Cl     H      H    H       --      CH.sub.3                            31 H  H        H      H    H       --      CH.sub.3                            31 H  H        H      H    H       --      OCH.sub.3                           32 H  H        H      H    H       H       CH.sub.3                            32 H  H        H      H    H       H       OCH.sub.3                           32 H  H        H      H    4-CH.sub.3                                                                             H       OCH.sub.3                           33 H  H        H      H    H       --      CH.sub.3                            33 H  H        H      H    H       --      OCH.sub.3                           33 H  H        H      H    2-CH.sub.3                                                                             --      OCH.sub.3                           34 H  H        H      H    2-CH.sub.3                                                                             --      OCH.sub.3                           34 H  H        H      H    H       --      OCH.sub.3                           34 H  H        H      H    H       --      CH.sub.3                            35 H  H        H      H    H       --      CH.sub.3                            35 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           35 H  H        H      H    H       --      OCH.sub.3                           35 CH.sub.3                                                                          H        H      H    H       --      OCH.sub.3                           35 H  H        CH.sub.3                                                                              H    H       --      OCH.sub.3                           35 H  H        H      CH.sub.3                                                                            H       --      OCH.sub.3                           36 H  H        H      H    H       --      CH.sub.3                            36 H  H        H      H    H       --      OCH.sub.3                           37 H  H        H      H    H       --      CH.sub.3                            37 H  H        H      H    H       --      OCH.sub.3                           38 H  H        H      H    H       --      OCH.sub.3                           38 H  H        H      H    CH.sub.3                                                                               --      OCH.sub.3                           39 H  H        H      H    H       --      CH.sub.3                            39 H  H        H      H    H       --      OCH.sub.3                           40 H  H        H      H    H       --      CH.sub.3                            40 H  H        H      H    H       --      OCH.sub.3                           41 H  H        H      H    4-Cl    --      CH.sub.3                            41 H  H        H      H    4-CN    --      CH.sub.3                            41 H  H        H      H    H       --      CH.sub.3                            41 H  H        H      H    H       --      OCH.sub.3                           42 H  H        H      H    4-Cl    --      OCH.sub.3                           42 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           42 H  H        H      H    H       --      CH.sub.3                            42 H  H        H      H    H       --      OCH.sub.3                           43 H  H        H      H    H       H       CH.sub.3                            43 H  H        H      H    H       H       OCH.sub.3                           43 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    3-Cl    5-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    3-CH.sub.3                                                                             5-CH.sub.3                                                                             OCH.sub.3                           43 H  H        H      H    4-N(CH.sub.3).sub. 2                                                                   H       OCH.sub.3                           43 H  H        H      H    5-CN    H       OCH.sub.3                           44 H  H        H      H    H       H       CH.sub.3                            44 H  H        H      H    H       H       OCH.sub.3                           45 H  H        H      H    H       H       CH.sub.3                            45 H  H        H      H    H       H       OCH.sub.3                           46 H  H        H      H    H       H       CH.sub.3                            46 H  H        H      H    H       H       OCH.sub.3                           46 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           46 H  H        H      H    5-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           47 H  H        H      H    H       H       CH.sub.3                            47 H  H        H      H    H       H       OCH.sub.3                           47 H  H        H      H    6-CH.sub.3                                                                             H       OCH.sub.3                           47 H  H        H      H    3-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           48 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           48 H  H        H      H    5-Cl    H       OCH.sub.3                           48 H  H        H      H    H       H       CH.sub.3                            48 H  H        H      H    H       H       OCH.sub.3                           49 H  H        H      H    H       H       CH.sub.3                            49 H  H        H      H    H       H       OCH.sub.3                           49 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             CH.sub.3                            49 H  H        H      H    4-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           49 H  H        H      H    4-OCH.sub.3                                                                            6-OCH.sub.3                                                                            CH.sub.3                            49 H  H        H      H    4-OCH.sub.3                                                                            6-OCH.sub.3                                                                            OCH.sub.3                           49 H  H        H      H    4-Cl    6-Cl    OCH.sub.3                           49 H  H        H      H    4-Cl    4-N(CH.sub.3).sub.2                                                                    OCH.sub.3                           49 H  H        H      H    4-OCH.sub.3                                                                            6-SCH.sub.3                                                                            OCH.sub.                            49 H  H        H      H    4-Cl    6-CN    OCH.sub.3                           50 H  H        H      H    H       H       CH.sub.3                            50 H  H        H      H    H       H       OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-OCH.sub.3                                                                            OCH.sub.3                           50 H  H        H      H    2-CH.sub.3                                                                             6-Cl    OCH.sub.3                           51 H  H        H      H    H       H       CH.sub.3                            51 H  H        H      H    H       H       OCH.sub.3                           51 H  H        H      H    2-CH.sub.3                                                                             H       OCH.sub.3                           51 H  H        H      H    5-CH.sub.3                                                                             H       OCH.sub.3                           51 H  H        H      H    OCH.sub.3                                                                              H       OCH.sub.3                           52 H  H        H      H    H       H       CH.sub.3                            52 H  H        H      H    H       H       OCH.sub.3                           52 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           52 H  H        H      H    CH.sub. 3                                                                              OCH.sub.3                                                                              OCH.sub.3                           52 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           53 H  H        H      H    H       H       CH.sub.3                            53 H  H        H      H    H       H       OCH.sub.3                           53 H  H        H      H    5-CH.sub.3                                                                             6-CH.sub.3                                                                             OCH.sub.3                           54 H  H        H      H    H       H       CH.sub.3                            54 H  H        H      H    H       H       OCH.sub.3                           55 H  H        H      H    H       H       CH.sub.3                            55 H  H        H      H    H       H       OCH.sub.3                           56 H  H        H      H    H       --      CH.sub.3                            56 H  H        H      H    H       --      OCH.sub.3                           56 H  H        H      H    6-CH.sub.3                                                                             --      OCH.sub.3                           57 H  H        H      H    H       --      OCH.sub.3                           57 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           58 H  H        H      H    H       --      OCH.sub.3                           58 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           59 H  H        H      H    H       --      CH.sub.3                            59 H  H        H      H    H       --      OCH.sub.3                           59 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           59 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           60 H  H        H      H    4-CH.sub.3                                                                             --      OCH.sub.3                           61 H  H        H      H    H       --      OCH.sub.3                           61 H  H        H      H    5-CH.sub.3                                                                             --      OCH.sub.3                           62 H  H        H      H    H       --      CH.sub.3                            62 H  H        H      H    H       --      OCH.sub.3                           63 H  H        H      H    H       --      CH.sub.3                            63 H  H        H      H    H       --      OCH.sub.3                           64 H  H        H      H    H       --      CH.sub.3                            64 H  H        H      H    H       --      OCH.sub.3                           65 H  H        H      H    H       --      OCH.sub.3                           66 H  H        H      H    H       --      OCH.sub.3                           67 H  H        H      H    H       --      CH.sub.3                            67 H  H        H      H    H       --      OCH.sub.3                           68 H  H        H      H    H       --      CH.sub.3                            68 H  H        H      H    H       --      OCH.sub.3                           69 H  H        H      H    H       --      CH.sub.3                            69 H  H        H      H    H       --      OCH.sub.3                           70 H  H        H      H    H       --      CH.sub.3                            70 H  H        H      H    H       --      OCH.sub.3                           71 H  H        H      H    H       H       CH.sub.3                            71 H  H        H      H    H       H       OCH.sub.3                           71 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            71 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           71 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           71 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           72 H  H        H      H    H       H       CH.sub.3                            72 H  H        H      H    H       H       OCH.sub.3                           72 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            72 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           72 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           72 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           73 H  H        H      H    H       H       CH.sub.3                            73 H  H        H      H    H       H       OCH.sub.3                           73 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            73 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           73 H  H        H      H    CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                           73 H  H        H      H    OCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                           74 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3                            74 H  H        H      H    CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                           32 H  H        H      H    H       H       Cl                                  32 H  H        H      H    H       H       H                                   35 H  H        H      H    H       --      Cl                                  35 H  H        H      H    H       --      H                                   ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE VIII                                                       ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74      1-10                                        Oil Suspensions,                                                                              3-50     40-95      0-15                                        Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84      1-20                                        Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9   0-15                                        High Strength 90-99      0-10     0-                                           Comparisons                                                                    ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 6

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                          80%                                                 aminosulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-                                benzamide                                                                      sodium alkylnaphthalenesulfonate                                                                          2%                                                  sodium ligninsulfonate     2%                                                  synthetic amorphous silica 3%                                                  kaolinite                  13%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 7

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       50%                                               aminosulfonyl]-N--(thiazol-2-yl)benzamide                                      sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth           46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 8

    ______________________________________                                         Granule                                                                        ______________________________________                                         Wettable Powder of Example 7                                                                           5%                                                     attapulgite granules   95%                                                     (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 9

    ______________________________________                                         Extruded Pellet                                                                ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       25%                                               aminosulfonyl]-N--(2-pyridinyl)benzamide                                       anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                                5%                                               sodium alkylnaphthalenesulfonate                                                                             1%                                               calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 10

    ______________________________________                                         Oil Suspension                                                                 ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar-                                                            25%                                                bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-                               benzamide                                                                      polyoxyethylene sorbitol hexaoleate                                                                         5%                                                highly aliphatic hydrocarbon oil                                                                           70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 11

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl-                                                     20%                                               pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-                                   benzamide                                                                      sodium alkylnaphthalenesulfonate                                                                            4%                                                sodium ligninsulfonate       4%                                                low viscosity methyl cellulose                                                                              3%                                                attapulgite                  69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 12

    ______________________________________                                         Low Strength Granule                                                           ______________________________________                                         2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                          1%                                                 carbonyl]aminosulfonyl]-N--(1-methyl-1H--pyrazol-                              3-yl)benzamide                                                                 N,N--dimethylformamide      9%                                                 attapulgite granules        90%                                                (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 13

    ______________________________________                                         Aqueous Suspension                                                             ______________________________________                                         N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl-                                                      40%                                              pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-                                   benzamide                                                                      polyacrylic acid thickener   0.3%                                              dodecylphenol polyethylene glycol ether                                                                     0.5%                                              disodium phosphate             1%                                              monosodium phosphate         0.5%                                              polyvinyl alcohol            1.0%                                              water                        56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 14

    ______________________________________                                         Solution                                                                       ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            5%                                                aminosulfonyl]-N--(1,2,4-triazol-3-yl)-                                        benzamide, sodium salt                                                         water                       95%                                                ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 15

    ______________________________________                                         Low Strength Granule                                                           ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                        0.1%                                             aminosulfonyl]-N--(thiazol-2-yl)benzamide                                      attapulgite granules         99.9%                                             (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 16

    ______________________________________                                         Granule                                                                        ______________________________________                                         2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                           80%                                               carbonyl]aminosulfonyl]-N--(1-methyl-1H--pyrazol-                              3-yl)benzamide                                                                 wetting agent                 1%                                               crude ligninsulfonate salt (containing                                                                      10%                                               5-20% of the natural sugars)                                                   attapulgite clay              9%                                               ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 17

    ______________________________________                                         High Strength Concentrate                                                      ______________________________________                                         2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                                                             99%                                               aminosulfonyl]-N--(1,2,4-triazol-3-yl)-                                        benzamide                                                                      silica aerogel              0.5%                                               synthetic amorphous silica  0.5%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 18

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                         90%                                             aminosulfonyl]-N--(2-pyridinyl)benzamide                                       dioctyl sodium sulfosuccinate 0.1%                                             synthetic fine silica         9.9%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 19

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         2-[[(4-methoxy-6-methylpyzimidin-2-yl)aminocar-                                                            40%                                                bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-                               benzamide                                                                      sodium ligninsulfonate      20%                                                montmorillonite clay        40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 20

    ______________________________________                                         Oil Suspension                                                                 ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                           35%                                                aminosulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-                                benzamide                                                                      blend of polyalcohol carboxylic                                                                             6%                                                esters and oil soluble petroleum                                               sulfonates                                                                     xylene                      59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

Utility

The compounds of the present invention are powerful herbicides. They have utility for broadspectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds are useful for the selective control of weeds in crops such as wheat and alfalfa.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.125 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rates for response to treatment.

The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

I=increased chlorophyl;

S=albinism;

U=unusual pigmentation;

X=axillary stimulation; and

6Y=abscised buds or flowers.

The ratings for the compounds tested by this procedure are presented in Table A.

Some of the compounds included in this table, e.g. compounds 1, 3, 4 and 6, were relatively inactive at the very low rates of applications selected, i.e. 0.05 kg/ha. It can reasonably be expected that they would have performed better at higher treatment levels.

                  TABLE A                                                          ______________________________________                                         Structures                                                                     ______________________________________                                          ##STR98##                Compound 1                                            ##STR99##                Compound 2                                            ##STR100##               Compound 3                                            ##STR101##               Compound 4                                            ##STR102##               Compound 5                                            ##STR103##               Compound 6                                            ##STR104##               Compound 7                                            ##STR105##               Compound 8                                            ##STR106##               Compound 9                                            ##STR107##               Compound 10                                           ##STR108##               Compound 11                                           ##STR109##               Compound 12                                           ##STR110##               Compound 13                                           ##STR111##               Compound 14                                           ##STR112##               Compound 15                                           ##STR113##               Compound 16                                           ##STR114##               Compound 17                                           ##STR115##               Compound 18                                           ##STR116##               Compound 19                                           ##STR117##               Compound 20                                           ##STR118##               Compound 21                                           ##STR119##               Compound 22                                           ##STR120##               Compound 23                                          ______________________________________                                    

                                      TABLE A                                      __________________________________________________________________________                  Cmpd. 1                                                                             Cmpd. 2                                                                              Cmpd. 3                                                                              Cmpd. 4                                                                             Cmpd. 5                                                                              Cmpd. 6                                                                              Cmpd. 7                                                                             Cmpd.                                                                               Cmpd. 9               Rate kg/ha   0.05 0.05  0.05  0.05 0.05  0.05  0.05 0.05 0.05                  __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean    2G   4C,9G,6Y                                                                             0     0    6C,9G,6Y                                                                             0     9C   9C   0                     Cotton       1H   2C,6G 0     2H   4C,9G 0     5C,9G                                                                               4C,9G                                                                               0                     Morningglory 2H   4C,7G 3G    1H   2C,8G 0     2C,5G                                                                               2C,9H                                                                               0                     Cocklebur    1H   3C,6G 0     1H   2H,4G 0     2C,9G                                                                               1C,9H                                                                               0                     Cassia       0    2C    0     0    2C,5G 0     5C,9G                                                                               5C,9G                                                                               0                     Nutsedge     0    0     0     0    1C,9G 0     9G   2C,9G                                                                               4G                    Crabgrass    0    0     0     0    1C,5G 0     2C,9G                                                                               2C,8G                                                                               1C,5G                 Barnyardgrass                                                                               0    5G    0     0    9H    0     5C,9G                                                                               5C,9H                                                                               1C,5G                 Wild Oats    0    0     0     0    6G,5X 0     9G   2C,9G                                                                               0                     Wheat        0    0     0     0    6G    0     2C,9G                                                                               1C,9G                                                                               0                     Corn         0    0     0     0    3U,9H 0     5U,9G                                                                               2U,9H                                                                               1C,4G                 Soybean      2C,5G                                                                               1H,2C,6G                                                                             1H    0    4C,9G 0     9C   9C   1H                    Rice         0    2C    0     0    4C,9G 0     5C,9G                                                                               5C,9G                                                                               1C,5G                 Sorghum      0    2C    0     0    2C,9G 0     3C,9G                                                                               2C,9G                                                                               1C,9G                 __________________________________________________________________________                 Cmpd. 10                                                                             Cmpd. 11                                                                             Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                             Cmpd. 15                                                                             Cmpd. 16                                                                             Cmpd.                                                                               Cmpd. 18              Rate kg/ha  0.05  0.05  0.05 0.05 0.4   0.05  0.05  0.05 0.05                  __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean   6C,9G,6Y                                                                             5C,9G,6Y                                                                             4S,8G,6Y                                                                            9C   8D,9G,6Y                                                                             9C    5C,9G,6Y                                                                             9C   10D,9G                Cotton      5C,9G 1U,4C,9G                                                                             2C,7G                                                                               4C,9G                                                                               9G    2U,3C,9G                                                                             3C,9G 4C,8G                                                                               2U,5C,9G              Morningglory                                                                               5C,9G 1C,3G 1C,6G                                                                               2C,5G                                                                               --    10C   5G    2C,8G                                                                               2C                    Cocklebur   1H    2C,8G 0    4C,9G                                                                               4G    2C,8G 6G    4G   5C,9G                 Cassia      2C    1C,5G 2C   6G   9G    6C,9G 4G    2G   5C,8G                 Nutsedge    1C    5C,9G 0    9G   9G    2C,4G 2C,9G 8G   9G                    Crabgrass   0     2C,8G 0    2C,8G                                                                               5G    2C    1C,9G 5G   1C,9G                 Barnyardgrass                                                                              0     6C,9H 0    3C,9H                                                                               --    2C    2C,9H 3C,9H                                                                               2C,9H                 Wild Oats   0     1C,8G 0    2C,9G                                                                               --    1C    9G    1C,5G                                                                               1C,9H                 Wheat       0     5C,9G 0    2C,9G                                                                               9G    1C    9G    1C,5G                                                                               9G                    Corn        2C,6H 5U,9G 0    5U,9G                                                                               9C    3C,9H 1C,9G 2C,9H                                                                               3U,9G                 Soybean     2C,7G 3C,9G 1C,1H                                                                               6C,9G                                                                               9G    9C    2C,7H 2C,9G                                                                               5C,9G                 Rice        0     9C    0    6C,9G                                                                               9G    2C,7G 9G,5I 2C,9G                                                                               4C,9G                 Sorghum     1C,8H 9C    0    2U,9G                                                                               9C    3C,8H 9G,5I 1C,9G                                                                               5U,9G                 __________________________________________________________________________                                         Cmpd. 19                                                                             Cmpd. 20                                                                             Cmpd. 21                                                                            Cmpd.                                                                               Cmpd. 23                                         Rate kg/ha                                                                             0.05  0.05  0.05 0.05 0.05                 __________________________________________________________________________                                 POST-EMERGENCE                                                                 Bush bean                                                                              9D,9C,6Y                                                                             9C    6C,9G                                                                               9C   7C,9G                                            Cotton  2C,3H,9G                                                                             2U,5C,9G                                                                             6C,9G                                                                               6C,9G                                                                               4C,9G                                            Morningglory                                                                           1C,4G 2C,8G 2C   9C   3C,5G                                            Cocklebur                                                                              2G    2G    4C,9G                                                                               5C,9G                                                                               1C,4G                                            Cassia  2C,4G 4C,6G 1C,3G                                                                               5C,9G                                                                               2C                                               Nutsedge                                                                               7G    0     5C,9G                                                                               8G   2C,8G                                            Crabgrass                                                                              5G    0     3C,9G                                                                               2C,8G                                                                               2C,8G                                            Barnyardgrass                                                                          5C,9H 0     9C   10C  3C,9H                                            Wild Oats                                                                              5G    0     9G   9G   4C,9G                                            Wheat   6G    0     4C,9G                                                                               5C,6G                                                                               2C,8G                                            Corn    2C,9H 1C,5H 5U,9G                                                                               5U,9C                                                                               2C,9H                                            Soybean 2C,8G 2C,9G 6C,9G                                                                               9C   6C,9G                                            Rice    1C,9G 4G    2C,9G                                                                               5C,9G                                                                               2C,9G                                            Sorghum 9G    2C,9G 5C,9G                                                                               9C   2C,9G                __________________________________________________________________________                  Cmpd. 1                                                                             Cmpd. 2                                                                              Cmpd. 3                                                                              Cmpd. 4                                                                             Cmpd. 5                                                                              Cmpd. 6                                                                              Cmpd. 7                                                                             Cmpd.                                                                               Cmpd. 9               Rate kg/ha   0.05 0.05  0.05  0.05 0.05  0.05  0.05 0.05 0.05                  __________________________________________________________________________     PRE-EMERGENCE                                                                  Morningglory 0    3C,5H 0     1C   8G    0     9G   9H   0                     Cocklebur    0    2C    0     0    9H    0     9G   9H   9H                    Cassia       0    2C    0     0    5G    0     7G   8G   1C                    Nutsedge     0    0     0     0    10E   0     10E  9G   2G                    Crabgrass    0    2G    0     0    3C    0     5G   5G   0                     Barnyardgrass                                                                               0    1C    0     0    2C,9H 0     2C,9H                                                                               3C,9H                                                                               2G                    Wild Oats    0    3G    0     0    2C,7G 0     2C,8G                                                                               2C,8G                                                                               2G                    Wheat        0    2G    0     0    1C,8G 0     9H   1C,9G                                                                               2G                    Corn         0    2C    0     1C   3C,8G 0     3C,9G                                                                               3C,9G                                                                               1C,6G                 Soybean      0    2C    0     0    1C,5H 0     7H   2C,7H                                                                               0                     Rice         0    2C    0     0    9H    0     10E  10E  1C,3G                 Sorghum      0    2C,5G 0     0    1C,8G 0     5C,9H                                                                               2U,9G                                                                               1C,5H                 __________________________________________________________________________                 Cmpd. 10                                                                             Cmpd. 11                                                                             Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                             Cmpd. 15                                                                             Cmpd. 16                                                                             Cmpd.                                                                               Cmpd. 18              Rate kg/ha  0.05  0.05  0.05 0.05 0.4   0.05  0.05  0.05 0.05                  __________________________________________________________________________     PRE-EMERGENCE                                                                  Morningglory                                                                               9G    9G    4G   9G   9G    9G    9G    9G   9G                    Cocklebur   9H    9H    5H   9H   --    9H    9H    9H   9H                    Cassia      1C    1C,5G 0    6G   9G    3C,9G 7G    8G   8G                    Nutsedge    0     8G    0    10E  10E   10E   10E   10E  10E                   Crabgrass   0     1C,5G 0    2C,8G                                                                               2C,8G 3G    3C,7G 1C,5G                                                                               1C,5G                 Barnyardgrass                                                                              1C    1C,9H 0    2C,9H                                                                               3C,9G 2C,4G 2C,9G 5C,9H                                                                               3C,9H                 Wild Oats   0     1C,8G 0    1C,9G                                                                               1C,8G 1C    9G    1C,9G                                                                               2C,9G                 Wheat       0     9G    0    9G   1C,9G 0     9G    9G   9G                    Corn        1C,6G 1U,9G 1C   2C,9G                                                                               1U,9G 2C,6G 3C,9G 2C,9G                                                                               9G                    Soybean     1C,2H 2C,6H 1H   6H   9H    2C,4H 7H    8H   9H                    Rice        1C,3G 9H    0    10E  10E   2C,5H 10E   10E  10E                   Sorghum     1C,5G 1C,9G 0    5C,9H                                                                               9H    2C,7G 5C,9H 2U,9G                                                                               6C,9H                 __________________________________________________________________________                                         Cmpd. 19                                                                             Cmpd. 20                                                                             Cmpd. 21                                                                            Cmpd.                                                                               Cmpd. 23                                         Rate kg/ha                                                                             0.05  0.05  0.05 0.05 0.05                 __________________________________________________________________________                                 PRE-EMERGENCE                                                                  Morningglory                                                                           9G    9G    9G   9G   9G                                               Cocklebur                                                                              9H    7H    9H   9H   8H                                               Cassia  8G    7G    8G   9G   7G                                               Nutsedge                                                                               9G    0     10E  10E  10E                                              Crabgrass                                                                              2C,4G 1C    1C,7G                                                                               2C,8G                                                                               5G,1C                                            Barnyardgrass                                                                          9C    1C    4C,9H                                                                               5C,9H                                                                               2C,9G                                            Wild Oats                                                                              2C,9G 0     2C,8G                                                                               2C,9H                                                                               2C,8G                                            Wheat   1C,9G 0     1C,9H                                                                               2C,9H                                                                               2C,9G                                            Corn    1C,9G 1C,4G 10E  9G   8G                                               Soybean 1C,5G 1C,3G 5H   9H   2C,6H                                            Rice    10E   2C,4G 10E  10E  4C,9H                                            Sorghum 2U,9G 2C    5C,9H                                                                               5C,9H                                                                               9G                   __________________________________________________________________________

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Note that certain compounds have relative tolerance for wheat.

                                      TABLE B                                      __________________________________________________________________________     PRE-EMERGENCE ON                                                               FALLSINGTON SILT LOAM                                                          __________________________________________________________________________                                                              Com-                           Compound 5                                                                             Compound 7                                                                             Compound 8                                                                             Compound 11                                                                            Compound 13                                                                            Compound                                                                               pound 17              Rate kg/ha                                                                              .060                                                                               .250                                                                               .030                                                                               .120                                                                               .030                                                                               .120                                                                               .060                                                                               .250                                                                               .030                                                                               .120                                                                               0.25                                                                               0.0625                                                                             0.25                  __________________________________________________________________________     Crabgrass                                                                               0   0   0   4G,2H                                                                              0   4G  0   6G  0   3G  8G,3H                                                                              7G,3H                                                                              6G,3H                 Barnyardgrass                                                                           4C,6G                                                                              5C,7G                                                                              5G,3H                                                                              7G,5H                                                                              6G,2H                                                                              8G,6C                                                                              7G,5H                                                                              9G,9C                                                                              3G  5G  8G,9C                                                                              8G,8C                                                                              8G,8C                 Sorghum  7G,5H                                                                              8G,5H                                                                              8G,5H                                                                              10C 6G,3H                                                                              8G  8G,8C                                                                              10C 5G,3H                                                                              9G,9C                                                                              10E 10C 9C,9G                 Wild Oats                                                                               5G  6G,3H                                                                              5G  7G  5G  7G  7G,3H                                                                              7G,6C                                                                              4G  6G,3H                                                                              6G,3C                                                                              6G,3H                                                                              6G,3H                 Johnsongrass                                                                            3G  7G,3H                                                                              7G,5H                                                                              7G,5H                                                                              4G,3H                                                                              7G,5H                                                                              6G,3H                                                                              7G,5H                                                                              4G  7G,5H                                                                              8G,5H                                                                              5H,7G                                                                              7G,5H                 Dallisgrass                                                                             0   4G  2G  5G  0   4G  6G  8G,3H                                                                              2G  6G  7C,8G                                                                              8G,3H                                                                              6G                    Giant foxtail                                                                           0   7G,5H                                                                              2G  5G,3H                                                                              4G,3H                                                                              7G,3H                                                                              7G,5H                                                                              9G,5H                                                                              0   3G,2H                                                                              8G,9C                                                                              7G,5C                                                                              7G,6C                 Ky. bluegrass                                                                           5G,3H                                                                              6G,3H                                                                              6G,3H                                                                              6G,3H                                                                              5G  6G,3H                                                                              7G,7C                                                                              8G,8C                                                                              6G  7G  8G,8C                                                                              8G,7C                                                                              8G,8C                 Cheatgrass                                                                              8G,8C                                                                              10C 7G  7G  6G  7G,5E                                                                              8G,9C                                                                              10E 8G  8G  10C 10C 7G,8C                 Sugar beets                                                                             7G,8C                                                                              9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              8G,7C                                                                              9G,9C                                                                              7G,8C                                                                              9G,9C                                                                              6G,4C                                                                              8G,8C                                                                              8G,9C                                                                              8G,8C                                                                              8G,8C                 Corn     0   8G,5H                                                                              7G,5H                                                                              10C 3G  6G,3H                                                                              3H  7G,5H                                                                              3G  3G  9G,9C                                                                              9G,9C                                                                              5G,5H                 Mustard  10C 10C 8G,6C                                                                              9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              9G,8C                                                                              10C 7G,6C                                                                              9G,9C                                                                              10C 8G,8C                                                                              9G,9C                 Cocklebur                                                                               5G  5G,3H                                                                              6G  7G,5H                                                                              3G  7G  3G  6G,3H                                                                              6G,5C                                                                              6G,2C                                                                              7G  5G  6G                    Pigweed  6G,5C                                                                              8G,8C                                                                              --  --  --  --  9G,9C                                                                              10C --  --  10C 10C 9G,9C                 Nutsedge 9G  8G  10E 10E 0   10E 3G  10E 9G  10E 10E 8G  3G                    Cotton   8G,5C                                                                              7G  8G,8C                                                                              9G,9C                                                                              0   8G,8C                                                                              2G  9G,8C                                                                              7G,3H                                                                              8G,5H                                                                              9G  7G  7G                    Morningglory                                                                            7G  8G  5G  7G  0   8G  5G  8G,5C                                                                              7G  8G  9G,5C                                                                              7G,3C                                                                              9G,8C                 Cassia   8G,3C                                                                              7G,3C                                                                              5G  5G  0   7G  4G,3C                                                                              7G,3C                                                                              5G  7G,5C                                                                              6G  3G  7G                    Teaweed  4G  4G  0   5C,7G                                                                              0   7G,3C                                                                              4G  6G  4G  7G,4C                                                                              6G,3C                                                                              3G  5G                    Velvetleaf                                                                              6G,3H                                                                              7G,6C                                                                              8G,5H                                                                              9G,9C                                                                              6G,5H                                                                              10C 8G,5H                                                                              8G,7C                                                                              6G,3H                                                                              7G,5H                                                                              9G,5H                                                                              8G,5H                                                                              6G,3H                 Jimsonweed                                                                              4G,4C                                                                              7G,6C                                                                              0   5G,3C                                                                              0   5G,5C                                                                              5G,3C                                                                              7G,5C                                                                              0   3G,3C                                                                              6G,3C                                                                              4G  6G,4C                 Soybean  4G,3H                                                                              6G,3H                                                                              4G  7G,5H                                                                              4G  8G,8C                                                                              3G,2C                                                                              9G,8C                                                                              3G,3H                                                                              5G,3H                                                                              7G,5H                                                                              4G,1C                                                                              5H,7G                 Rice     7G,5H                                                                              10C 10E 10E 7G  10E 8G,8C                                                                              10C 9G,9C                                                                              10C 10E 10E 7G,5H                 Wheat    4G  5G  4G  7G,3H                                                                              3G  6G,3H                                                                              4G  7G,5C                                                                              3G  4G  7G,3C                                                                              6G,2C                                                                              5G                    __________________________________________________________________________              Com-                                                                           pound 17                                                                             Compound 18                                                                              Compound 19                                                                              Compound 20                                                                             Compound 21                                                                              Compound 22              Rate kg/ha                                                                              0.0625                                                                               0.12 0.0312                                                                              0.12 0.0312                                                                              0.12 0.0312                                                                             0.12 0.0312                                                                              0.12 0.0312              __________________________________________________________________________     Crabgrass                                                                               5G,2H 6G   5G   3G   0    0    0   7G   4G   5G   3G                  Barnyardgrass                                                                           7G,5C 8G,8C                                                                               8G,3C                                                                               7G,5C                                                                               5G,2C                                                                               0    0   8G   5G   8G,3H                                                                               6G,2H               Sorghum  7G,5H 10C  9G,9C                                                                               7G,3H                                                                               6G,3H                                                                               3G   0   10C  7G,3H                                                                               9G,9C                                                                               9G,3H               Wild Oats                                                                               5G    6G,6C                                                                               6G,3C                                                                               6G,2H                                                                               4G   0    0   7G   4G   7G,3H                                                                               4G                  Johnsongrass                                                                            3H,4G 8G,8C                                                                               8C,8G                                                                               7G,5H                                                                               4G,3H                                                                               0    0   7G   3G   8G   7G                  Dallisgrass                                                                             5G    3H,8G                                                                               7G,3H                                                                               4G   3G   0    0   5G   0    5G   2G                  Giant foxtail                                                                           6G,3C 8G,5H                                                                               8G,5H                                                                               6G,3H                                                                               4G   0    0   5G,3H                                                                               0    8G,5H                                                                               4G                  Ky. bluegrass                                                                           7G    7G,8C                                                                               7G,8C                                                                               6G   5G   3G   0   6G   5G   6C,6G                                                                               5G                  Cheatgrass                                                                              10C   10E  10E  7G,8C                                                                               6G   0    0   9G,9C                                                                               7G   10E  5G                  Sugar beets                                                                             8G,8C 9G,9C                                                                               7G,7C                                                                               8G,8C                                                                               6G,5C                                                                               8G,8C                                                                               8G,8C                                                                              7G,7C                                                                               6G,5H                                                                               8G,8C                                                                               6G,3H               Corn     3G    10E  10E  8C,8G                                                                               4G   2G   0   6G,5H                                                                               0    4G   0                   Mustard  8G,8C 10C  8G,5C                                                                               9G,8C                                                                               5C,8G                                                                               7G,5C                                                                               5G  9G,9C                                                                               8G,8C                                                                               9G,9C                                                                               8G,8C               Cocklebur                                                                               3G    8G,5C                                                                               6G   6G   5G   6G   7G  5G,3H                                                                               5G   2G   --                  Pigweed  10C   10C  7G   7G,6C                                                                               3G   6G   0   --   --   --   --                  Nutsedge 3G    10E  10E  7G   5G   3G   0   10E  2G   3G   0                   Cotton   6G    9G,5H                                                                               9G,5H                                                                               3H,6G                                                                               0    9G,3H                                                                               7G,3H                                                                              3H,7G                                                                               3G   5G,5H                                                                               4G,3H               Morningglory                                                                            5G    8G,5C                                                                               7G,3C                                                                               7G,5H                                                                               3G   8G,3H                                                                               5G  7G,3H                                                                               3H   3G   4G                  Cassia   5G    5G   5G   4G   3G   5G   4G  7G,3C                                                                               3G   6G   6G                  Teaweed  0     7G   5G   4G   3G   3G   2G  10E  3G   6G,3C                                                                               4G                  Velvetleaf                                                                              5G,3H 9G,5C                                                                               8G,3H                                                                               6G,5H                                                                               4G,3H                                                                               2G   3G  7G,8C                                                                               5G,3H                                                                               5G,5H                                                                               4G,3H               Jimsonweed                                                                              3G,4C 9G,8C                                                                               5G,3C                                                                               5G   2G   4G   3G  6G,3C                                                                               4G   4G,3C                                                                               3G                  Soybean  5G,2H 8G,5H                                                                               7G,5H                                                                               6G,5H                                                                               2H   5G,1C                                                                               2G  5G,3H                                                                               2G   3G   4G                  Rice     7G,5H 10E  10E  7G   5G   0    0   10E  10E  10E  7G                  Wheat    4G    7G   7G,3C                                                                               4G   2G   0    0   4G   0    3G   3G                  __________________________________________________________________________                                                    Compound                                                                               Compound 14                                                    Rate kg/ha                                                                             0.12                                                                               0.0312                                                                             0.25                                                                               0.06                __________________________________________________________________________                                            Crabgrass                                                                              0   0   3H  0                                                          Barnyardgrass                                                                          5G  0   5G,3H                                                                              0                                                          Sorghum 7G,5H                                                                              2G  8G,5H                                                                              5G,5H                                                      Wild Oats                                                                              4G  0   4G  0                                                          Johnsongrass                                                                           3G  0   6G,3H                                                                              0                                                          Dallisgrass                                                                            3G  0   0   0                                                          Giant foxtail                                                                          3G  0   0   0                                                          Ky. bluegrass                                                                          5G  0   8G,8C                                                                              5G,5H                                                      Cheatgrass                                                                             0   0   3G,3H                                                                              3G                                                         Sugar beets                                                                            7G,6C                                                                              4G  7G,8C                                                                              6G,7C                                                      Corn    0   0   3G  0                                                          Mustard 9G,9C                                                                              6G,5C                                                                              9G,9C                                                                              6G,5E                                                      Cocklebur                                                                              3G  0   4G  0                                                          Pigweed --  --  10C 7G,9E                                                      Nutsedge                                                                               7G  0   3G  0                                                          Cotton  3G  0   8G  2G                                                         Morningglory                                                                           3G  3G  8G  4G                                                         Cassia  5G  0   8G  0                                                          Teaweed 2G  0   5G  0                                                          Velvetleaf                                                                             5G,3H                                                                              0   6G  0                                                          Jimsonweed                                                                             3G  0   7G,7C                                                                              0                                                          Soybean 2G  0   0   0                                                          Rice    7G,7C                                                                              3G  8G,3H                                                                              6G                                                         Wheat   2G  0   3G  0                   __________________________________________________________________________

Test C

Twenty-five cm diameter plastic pots filled with Fallsington slit loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. Note that one compound is especially tolerant to alfalfa.

                                      TABLE C                                      __________________________________________________________________________     POST-EMERGENCE                                                                 Over-the-Top Soil/Foliage Treatment                                            __________________________________________________________________________                                                              Com-                           Compound 5                                                                              Compound 7                                                                               Compound 8                                                                              Compound 11 Compound                                                                               pound 15              Rate kg/ha                                                                              0.06 0.0125                                                                             0.06 0.0125                                                                              0.06                                                                               0.0125                                                                              0.06                                                                               0.0125                                                                              0.006                                                                             0.06                                                                               0.0125                                                                             0.06                  __________________________________________________________________________     Soybeans 10G,7C                                                                              8G,5C                                                                              10G,8C                                                                              10G,3C                                                                              9G,6C                                                                              10G,5C                                                                              10C 8G,5C                                                                               2C 9G,2C                                                                              5G  10G,7C                Velvetleaf                                                                              9G,8C                                                                               6G  10C  9G   10C 7G   10C 10C  0  9G,4C                                                                              2G,2C                                                                              9G,8C                 Sesbania 9G,3C                                                                               7G  9G,3C                                                                               8G   10C 8G   10C 10C  4G 8G  2G  9G,9C                 Cassia   9G,3C                                                                               3G  8G   4G   8G  5G   9G,9C                                                                              9G,9C                                                                               2C 2C  0   9G,8C                 Cotton   8G   6G  10G  7G   10G 9G,5C                                                                               9G,9C                                                                              9G,9C                                                                               2C 8G  2G  10G                   Morningglory                                                                            9G   3G  9G,6C                                                                               8G   9G,9C                                                                              8G   9G,9C                                                                              9G,9C                                                                               2G 9G  4G  9G,5C                 Alfalfa  9G,5C                                                                               2G  6G   9G   10C 8G   10C 10C  4G 3G  0   10C                   Jimsonweed                                                                              0    0   9G   0    10C 7G   9G,4C                                                                              9G,2C                                                                               5G 0   2C  10C                   Cocklebur                                                                               0    0   8G   5G   8G  5G   9G  6G   0  5G  2C  8G                    Sunflower                                                                               4G   0   8G,2H                                                                               6G   8G  5G   9G,9C                                                                              7G   2C 4G  4G  10C                   Mustard  9G   9G  9G,9C                                                                               9G   10C 9G   10C 10C  0  9G  7G  10C                   Sugar beets                                                                             8G   5G,3C                                                                              8G   9G   10C 9G,8C                                                                               10C 9G,4C                                                                               3G 9G  4G  9G,9C                 Corn     8G,3U                                                                               8G,3U                                                                              9G,9U                                                                               9G,9C                                                                               10C 7G,3U                                                                               9G,9C                                                                              9C,3C                                                                               4G 8G,3U                                                                              8G,1H                                                                              7G,3U                 Crabgrass                                                                               0    4C  4G   0    0   0    2G  0    0  2G  0   0                     Rice     4G,2C                                                                               4G  7G,3C                                                                               7G,3C                                                                               6G,5C                                                                              4G   10C 9G,8C                                                                               0  8G  8G  0                     Nutsedge 8G   9C  7G   9C   10C 3G,3C                                                                               9G,9C                                                                              9G,9C                                                                               0  8G,7C                                                                              7G  0                     Barnyardgrass                                                                           7G   5G  9G,9C                                                                               8G,8C                                                                               10C 8G   9G,8C                                                                              9G,2U                                                                               3G 9G,2H                                                                              6G  0                     Wheat    0    0   9G,2C                                                                               5G   5G,2C                                                                              3G   7G,5U                                                                              6G,4C                                                                               0  7G,3C                                                                              5G  0                     Giant foxtail                                                                           0    0   8G   4G   9G  5G   9G,2U                                                                              8G   2G 6G  0   0                     Wild Oats                                                                               4G,4C                                                                               2C  9G,9C                                                                               7G   6G,2C                                                                              2G   10C 7G,2C                                                                               0  7G,3C                                                                              6G,2C                                                                              0                     Sorghum  7G   6G  8G,8C                                                                               7G,2U                                                                               7G  6G   10C 8G,6C                                                                               4G 7G  7G  4G                    Johnsongrass                                                                            5G   5G  9G,8C                                                                               9G,2U                                                                               10C 9G,3U                                                                               --  --   5G 9G,2U                                                                              4G  0                     Field Bindweed                                                                          5G   4G  7G   0    10C 6G   --  --   2C 0   2G  10C                   __________________________________________________________________________              Compound 15                                                                            Compound 16                                                                            Compound 17 Compound 18     Compound 21                        0.0125                                                                              0.006                                                                             .063                                                                               .016                                                                               .250                                                                               .063                                                                               .016                                                                               0.06                                                                               0.0125                                                                             0.006                                                                              0.006                                                                              0.06                                                                               0.0125                __________________________________________________________________________     Soybeans 10G,3C                                                                              6G 8G  8G  9G  6G  6G  10G,6C                                                                             8G  9G  5G  10C 10G,5C                Velvetleaf                                                                              5G,2C                                                                               6G 9G,7C                                                                              8G,4C                                                                              9G,9C                                                                              7G,5C                                                                              7G  9G  8G  5G  4G  9G,8C                                                                              6G                    Sesbania 5G   7G 8G  7G,5C                                                                              9G,8C                                                                              7G,2C                                                                              7G  9G  2G  4G  8G  9G,8C                                                                              6G                    Cassia   9G,6C                                                                               0  2C  3G,2C                                                                              9G,7C                                                                              9G,7C                                                                              6G  9G  5G,3C                                                                              0   0   8G  2G                    Cotton   8G,3C                                                                               6G 6G  2G  8G,3C                                                                              7G,2C                                                                              4G  9G,5C                                                                              2G  1C  5G  9G  3G                    Morningglory                                                                            7G   7G 2G  0   9G,7C                                                                              8G,7C                                                                              8G,5C                                                                              3G  4G  0   4G  9G  0                     Alfalfa  9G   6G 2C  2C  10C 8G,7C                                                                              6G,3C                                                                              2G,2C                                                                              0   4G  0   9G,5C                                                                              0                     Jimsonweed                                                                              4G   2G 5G  5G  7G  8G  2G  9G  6G  8G,2C                                                                              0   7G  0                     Cocklebur                                                                               2G   4G 8G  7G  8G  8G  4G  7G  6G  0   6G  8G  5G                    Sunflower                                                                               6G,2H                                                                               3G 5G  7G  8G,6C                                                                              4G,4C                                                                              6G,2C                                                                              8G,2H                                                                              4G  0   2C  8G,1H                                                                              3G                    Mustard  8G   4G 10C 10C 9G,9C                                                                              9G,9C                                                                              7G,2C                                                                              9G,5C                                                                              8G  5G  2G  10C 8G                    Sugar beets                                                                             5G   6G 9G  9G  9G,5C                                                                              9G,5C                                                                              8G  9G,5C                                                                              8G  5G  6G  10C 9G                    Corn     6G   2G 9G,5C                                                                              9G,5C                                                                              10C 9G,9C                                                                              9G,7C                                                                              8G,8C                                                                              8G,3C                                                                              8G,5H                                                                              6G,3H                                                                              10C 9G,7C                 Crabgrass                                                                               0    3G 10C 7G  6G,3C                                                                              2G  0   4G  0   0   0   7G  0                     Rice     0    0  7G,4C                                                                              7G,1C                                                                              9G,8C                                                                              7G  7G  9G,5C                                                                              7G  3G,2C                                                                              4G  10C 7G,7C                 Nutsedge 0    3G 6G  4G  10C 9C  2G  10C 10C 8G,2C                                                                              4G  7G,7C                                                                              5G,5C                 Barnyardgrass                                                                           0    2G 9G,4C                                                                              10C 9G,8C                                                                              8G  4G  9G,6C                                                                              10C 4G,2C                                                                              1G  10C 10C                   Wheat    0    0  8G,2C                                                                              8G,4C                                                                              9G,4C                                                                              9G,2C                                                                              2G  9G  6G  5G  1G  9G,8C                                                                              5G                    Giant foxtail                                                                           6G   0  8G  8G  8G,3C                                                                              8G  7G  8G  4G  0   4G  9G  8G                    Wild Oats                                                                               0    0  9G  8G,5C                                                                              9G,4C                                                                              8G  4G  9G,5C                                                                              5G  0   0   8G  6G                    Sorghum  0    2G 10C 8G,8C                                                                              8G,9C                                                                              8G,8C                                                                              7G  10C 7G,8C                                                                              6G  8G  10C 7G,3C                 Johnsongrass                                                                            3G   3G 9G,7U                                                                              8G,7U                                                                              9G,8C                                                                              7G,3U                                                                              4G  9G,8C                                                                              10C 5G,4U                                                                              5G  9G,8U                                                                              7G,3U                 Field Bindweed                                                                          8G   0  5G  --  5G  2G  0   5G  0   0   0   10C 2G                    __________________________________________________________________________                                         Compound 22       Compound 23                                          Rate kg/ha                                                                             0.06                                                                               0.0125                                                                             0.006                                                                               0.006                                                                               0.06 0.0125              __________________________________________________________________________                                 Soybeans                                                                               10C 10C 10G,3C                                                                              10G,5C                                                                              10G,6C                                                                              8G,6C                                           Velvetleaf                                                                             10C 8G,5C                                                                              7G,2C                                                                               10C  6G   2G                                              Sesbania                                                                               10C 10C 9G,8C                                                                               10G,6C                                                                              9G,5C                                                                               3G                                              Cassia  8G  9G,8C                                                                              5G,3C                                                                               4G   8G,2C                                                                               7G                                              Cotton  9G,5C                                                                              8G,2C                                                                              8G,2C                                                                               7G   9G,5C                                                                               7G                                              Morningglory                                                                           9G,8C                                                                              9G,7C                                                                              8G,2C                                                                               8G   5G   4G                                              Alfalfa 9G,9C                                                                              7G,5C                                                                              8G,2C                                                                               6G   8G,6C                                                                               5G                                              Jimsonweed                                                                             9G  9G  4G   3G   0    0                                               Cocklebur                                                                              8G  6G  4G   6G   3G   0                                               Sunflower                                                                              8G  5G  5G   10C  6G   1G                                              Mustard 10C 7G  8G   7G,3C                                                                               6G   8G                                              Sugar beets                                                                            10C 10C 1G   9G   5G   0                                               Corn    10C 10C 7G,8C                                                                               7G,3H                                                                               9G,5C                                                                               9G,3U                                           Crabgrass                                                                              4G,2C                                                                              3G  0    4G   0    0                                               Rice    10C 8G,8C                                                                              5G,5C                                                                               7G   7G,3C                                                                               2G                                              Nutsedge                                                                               10C 10C 7C   0    8G   3C                                              Barnyardgrass                                                                          10C 10C 6G,2C                                                                               7G,1H                                                                               10C  5G                                              Wheat   8G,6C                                                                              8G,2C                                                                              2G   2G   1G   0                                               Giant foxtail                                                                          9G,2C                                                                              9G  2G   3G   4G   4G                                              Wild Oats                                                                              9G,8C                                                                              9G  2G   0    6G   1C                                              Sorghum 10C 8G,3C                                                                              8G   7G   8G,5C                                                                               6G                                              Johnsongrass                                                                           10C 10C 6G,4C                                                                               7G,2H                                                                               9G,2U                                                                               7G                                              Field Bindweed                                                                         6G  9G  7G   3G   2G   2C                  __________________________________________________________________________ 

What is claimed is:
 1. A compound of the formula: ##STR121## wherein A is a five-membered aromatic heterocycle or a five-membered dihydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4 CH₃, 1-2 OCH₃, 0-1 SCH₃, 0-1 N(CH₃)₂, or 0-1 CN groups;R is H or CH₃ ; R₁ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ; R₂ is H or CH₃ ; R₃ is H or CH₃ ; R₄ is ##STR122## X is CH₃, OCH₃ or Cl; Y is H, CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ; and Z is Nprovided that (1) the bond between N-R and A is attached to a nitrogen or carbon atom of A; and (2) when A is a thiophene or furan ring, the bond between NR and A is not at the 2- or 5-position of the heterocycle.
 2. Compounds of claim 1 wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one to four nitrogen atoms.
 3. Compounds of claim 1 wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one or two nitrogen atoms and one oxygen or one sulfur atom.
 4. Compounds of claim 1 wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one oxygen or one sulfur atom.
 5. Compounds of claim 1 wherein A is an unsubstituted or substituted five-membered dihydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur.
 6. Compounds of claim 2 wherein ##STR123## Y is CH₃ or OCH₃ ; and
 7. Compounds of claim 6 wherein A is unsubstituted or optionally substituted with 0-4 CH₃ or 0-2 OCH₃ groups.
 8. Compounds of claim 7 wherein A is a pyrrole, an imidazole, a pyrazole, or a 1,2,4-triazole.
 9. Compounds of claim 3 wherein A is an isoxazole, an oxazole, a 1,3,4-oxadiazole, a thiazole, a 1,2,3-thiadiazole, or a 1,3,4-thiadiazole.
 10. Compounds of claim 7 wherein A is a 4,5-dihydroimidazole, a 4,5-dihydroisoxazole, a 4,5-dihydrooxazole, a 4,5-dihydropyrazole, or a 4,5-dihydrothiazole.
 11. Compounds of claim 8 wherein R, R₁, R₂ and R₃ are H, and A is unsubstituted, or, optionally substituted with one methyl group.
 12. The compound of claim 1 which is 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1-methyl-1H-pyrazol-3-yl)benzamide.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 17. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 